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US8796339B2 - Compositions comprising benzyl alcohol derivatives and further antimicrobial active compounds - Google Patents

Compositions comprising benzyl alcohol derivatives and further antimicrobial active compounds Download PDF

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US8796339B2
US8796339B2 US13/003,404 US200813003404A US8796339B2 US 8796339 B2 US8796339 B2 US 8796339B2 US 200813003404 A US200813003404 A US 200813003404A US 8796339 B2 US8796339 B2 US 8796339B2
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mixture
octanediol
hexanediol
acid
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US20110152383A1 (en
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Gerhard Schmaus
Antje Pfeiffer
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Symrise AG
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Symrise AG
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/046—Aerosols; Foams
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/062—Oil-in-water emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005—Antimicrobial preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/524—Preservatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/87—Application Devices; Containers; Packaging
    • A61K2800/874—Roll-on
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/004—Aftersun preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair

Definitions

  • the present invention relates to the field of antimicrobial actives, and in particular relates to certain (synergistic) antimicrobial compositions (mixtures) comprising or consisting of (a) at least one benzyl alcohol derivative as specified in more detail below and (b) at least one antimicrobial active compound selected from subgroups (i) to (xi) as specified in more detail below.
  • the most preferred benzyl alcohol derivative is 4-methylbenzyl alcohol.
  • constituent of group (b) most preferred are 1,2-alkanediols having 3 to 14 carbon atoms.
  • Other preferred compositions are described in more detail below and/or are defined in the attached set of claims.
  • the present invention further relates to the use of a composition according to the present invention for use in the treatment of germs, in particular for use in the treatment of Aspergillus niger.
  • composition according to the present invention for the preparation of a medicament for use in the treatment of germs, in particular for use in the treatment of Aspergillus niger.
  • a further aspect of the present invention relates to the use of (a) at least one benzyl alcohol derivative (as specified in more detail below) for synergistically intensifying the antimicrobial activity of certain antimicrobial actives (as specified in more detail below).
  • a corresponding method according to the present invention is a method for synergistically intensifying the antimicrobial activity of (b) one or more antimicrobial actives (as specified in more detail below), wherein said antimicrobial actives are mixed with an effective amount of (a) at least one benzyl alcohol derivative as specified in more detail below.
  • the present invention relates to a method for the preservation or antimicrobial treatment of a perishable product, wherein the perishable product is brought into contact with a composition according to the present invention.
  • All aspects of the present invention are based on the finding that it is possible to synergistically intensify the antimicrobial activity by combining at least one benzyl alcohol derivative of formula (I) (i.e. a compound of group (a)) (as specified below) with at least one compound of group (b), i.e. of sub-groups (i) to (xi) (as specified below).
  • agents having antimicrobial properties in particular for the preservation of products which are otherwise perishable (such as e.g. cosmetics, pharmaceutical products, oral care products, foodstuffs and beverages), but also for direct cosmetic or therapeutic treatment of microorganisms which can have an adverse influence on the human or animal body.
  • Aspergillus niger is a mould which can be combated only with great difficulty. Although substances like 1,2-alkanediols having 3 to 14 carbon atoms are known to have a considerable activity against certain germs and microorganisms, in a number of cases the effect against Aspergillus niger is considered to be not sufficient.
  • the alternative antimicrobial active or the antimicrobial additive should be essentially or completely odorless in typical concentrations of use.
  • the antimicrobial effect of the alternative antimicrobial active or the effect of the combination of the antimicrobial additive with the known antimicrobial active against Aspergillus niger should preferably be so strong that a product comprising 1 wt.-% of the antimicrobial active or the combination should allow for a 3 log or at least 2 log reduction of germs within one week (see the examples section below for further details of test design etc.).
  • composition comprising or consisting of
  • each of the substituents R 1 , R 2 , and R 3 has a position at the aromatic ring, and wherein the substituents R 1 , R 2 , and R 3 independently of one another are selected from the group consisting of: H; OH; OCH 3 ; COON; linear or branched, saturated aliphatic hydrocarbon radical having 1 to 8 carbon atoms; linear or branched, unsaturated aliphatic hydrocarbon radical having 2 to 8 carbon atoms; COOR 4 , wherein R 4 is a linear or branched alkyl radical having 1 to 8 carbon atoms; wherein the total number of carbon atoms in substituents R 1 , R 2 and R 3 is 1 to 12, and (b) one, two or more compounds selected from the group consisting of:
  • the invention is based on the surprising finding that (a) benzyl alcohol derivatives of the formula (I) as stated above (as antimicrobial additive) synergistically increase the antimicrobial activity of (b) compounds selected from sub-groups (i) to (xi) as stated above.
  • the antimicrobial mixtures according to the invention are suitable for preservation and antimicrobial treatment of perishable products, such as e.g. cosmetic products, pharmaceutical products, oral care products, foodstuffs and beverages.
  • the amounts and ratios of (a) the one or more benzyl alcohol derivatives of formula (I) and the one or more compounds of group (b) in the mixture according to the present invention are preferably adjusted such that their antimicrobial action is intensified synergistically according to Kull et al.; Applied Microbiology 9; p. 538-541 (1961), see also Steinberg; Cosmetics & Toiletries 115 (11); p. 59-62 (2000).subenter zu 29ieben
  • the only, one, two or more compounds of component (a) are selected from the group consisting of benzyl alcohol derivatives of said formula (I) wherein the substituents R 1 , R 2 , and R 3 independently of one another are selected from the group consisting of:
  • compositions according to the present invention wherein the only, one, two or more compounds of component (a) are selected from the group consisting of benzyl alcohol derivatives of said formula (I) wherein the substituents R 1 , R 2 , and R 3 independently of one another are selected from the group consisting of:
  • compositions according to the present invention wherein the only, one, two or more compounds of component (a) are selected from the group consisting of:
  • one or the only compound of component (a) is 4-methylbenzyl alcohol.
  • the concentration of component (a), i.e. the total concentration of compounds selected from the above defined group consisting of benzyl alcohol derivatives of the formula (I) (according to any of the above embodiments, in particular according to any of the embodiments characterized as being preferred) can vary and will largely depend on both the concentration of component (b) (total concentration of compounds selected from subgroups (i) to (xi)) and the concentration of further components.
  • concentration of component (a) will be higher than in compositions comprising a large amount of further components besides components (a) and (b).
  • compositions according to the present invention which comprise at least 50 wt.-% of further components besides (a) and (b), component (a) is present in an amount of from 0.05 to 0.50 wt.-%, preferably 0.10 to 0.30 wt.-%, based on the total weight of the composition.
  • component (a) is present in an amount of from 2 to 80 wt.-%, preferably 5 to 50 wt.-%, based on the total weight of component (b).
  • composition according to the present invention is a composition, wherein the total amount of compounds of component (b) or the total amount of one or more or all compounds selected from one of subgroups (i) to (xi) of component (b) is selected so as to synergistically intensify the antimicrobial activity of the total amount of compounds of component (a).
  • compositions according to the present invention comprise as component (b) one, two or more compounds selected from the group consisting of sub-groups (i) to (xi).
  • component (b) one, two or more compounds selected from the group consisting of sub-groups (i) to (xi).
  • the skilled person will understand that the amount of component (b) will depend on the compounds selected from sub-groups (i) to (xi), and their amounts.
  • compositions according to the present invention are preferred which comprise at least 50 wt.-% of further components besides (a) and (b), wherein component (a) is present in an amount of from 0.05 to 0.5 wt.-%, based on the total weight of the composition (see above).
  • component (a) is present in an amount of from 0.05 to 0.5 wt.-%, based on the total weight of the composition (see above).
  • compositions according to the present invention comprising at least 50 wt.-% of further components besides (a) and (b)) comprising one, two or more compounds and total amounts as selected from the group consisting of
  • compositions according to the present invention are preferred, wherein for one or more sub-groups (i) to (xi) of component (b) the ratio r a/b of the total weight of component (a) to the total weight of compounds of said sub-groups of component (b) is in the range of from
  • level range Antimicrobial range group (a): group (a): Agents [weight-%] group (b) group (b) 1,2-Alkanediols 0.1-5.0 1:100 to 5:1 1:20 to 1:1 Benzoic Acid 0.1-1.0 1:20 to 5:1 1:5 to 2:1 Parabens 0.1-0.8 1:16 to 5:1 1:4 to 2:1 Sorbic Acid 0.1-0.6 1:12 to 5:1 1:3 to 2:1 Phenoxyethanol 0.1-1.0 1:20 to 5:1 1:2 to 5:1 Chlorphenesin 0.02-0.2 1:4 to 25:1 1:2 to 10:1 Imidazolidinyl urea 0.1-0.6 1:12 to 5:1 1:3 to 2:1 Diazolidinyl Urea 0.1-0.5 1:10 to 5:1 1:3 to 2:1 DMDM hydantoin 0.1-0.6 1:12 to 5:1 1:3 to 2:1 Octoxyglycerin 0.1-1.0 1:20 to
  • compositions according to the present invention show a synergistically intensified antimicrobial effect at least against selected germs, and in particular at least against Aspergillus niger , a mould which can be combated only with great difficulty.
  • compositions according to the present invention can be used outstandingly as an antimicrobial active compound mixture (composition), in particular for preserving otherwise perishable articles (see the initial remarks above and the more detailed description below).
  • compositions according to the present invention could have a significantly improved antimicrobial action (at least against selected germs).
  • compositions according to the present invention As to the compounds of sub-groups (i) to (xi) of component (b) of compositions according to the present invention, various documents describe antimicrobial activity of the compounds per se. Regarding combinations of 1,2-alkanediols with further antimicrobially active substances, EP 1 206 933, WO 03/069994 and WO 2006/082151 may be mentioned by way of example. However, compositions according to the present invention and their antimicrobial activity, in particular against Aspergillus niger , are not disclosed in the prior art.
  • 1,2-alkanediols generally have only a deficient action against moulds such as Aspergillus niger .
  • moulds such as Aspergillus niger .
  • a gap in the activity is recorded with respect to moulds, in particular with respect to the “problem germ” Aspergillus niger .
  • concentrations of individual 1,2-alkanediols and their mixtures are necessary.
  • a synergistic intensification in antimicrobial activity by combination of (a) one, two or more benzyl alcohol derivatives of formula (I), in particular 4-methylbenzyl alcohol, with (b) (i) branched or unbranched 1,2-alkane diols having 3 to 14 carbon atoms is not disclosed in the prior art.
  • compositions according to the present invention show a highly synergistic activity, and in the treatment of Aspergillus niger are significantly superior to
  • compositions according to the present invention are particularly suitable for combating Aspergillus niger even at low concentration.
  • component (b) of the composition according to the present invention comprises or consists of one, two or more compounds selected from the group consisting of (i) branched or unbranched 1,2-alkanediols having 3 to 10 carbon atoms.
  • branched or unbranched 1,2-alkanediols having 3 to 10 carbon atoms from the group consisting of 1,2-propanediol, 1,2-butanediol, 1,2-pentanediol, 1,2-hexanediol, 1,2-octanediol, 1,2-decanediol, and mixtures thereof.
  • mixtures of said 1,2-alkanediols is in particular preferred.
  • compositions of the present invention component (b) comprise or consist of
  • composition component (a) comprises or consists of 4-methylbenzyl alcohol.
  • component (a) comprises or consists of 4-methylbenzyl alcohol
  • component (b) comprises or consists of a mixture of two different 1,2-alkanediols, preferably of a mixture of 1,2-hexanediol and 1,2-octanediol.
  • compositions of the present invention comprise two different 1,2-alkanediols, preferably two different 1,2-alkanediols, preferably a mixture of 1,2-hexanediol and 1,2-octanediol, in a weight ratio of from 10:1 to 1:10, preferably of from 5:1 to 1:5.
  • composition comprising both 1,2-hexanediol and 1,2-octanediol as well as 4-methylbenzyl alcohol
  • weight ratio of 4-methylbenzyl alcohol to the total amount of 1,2-hexandediol and 1,2-octanediol is preferably in the range of from 1:1 to 1:10, more preferably in the range of from 1:2 to 1:6.
  • a composition according to the present invention comprises a total amount of 8 parts by weight of one or more 1,2-alkanediols (in particular 1,2-hexanediol and/or 1,2-octanediol)
  • the total amount of benzyl alcohol derivatives of formula (I) in particular the total amount of 4-methylbenzyl alcohol, would preferably be in the range of 0.5 to 5 parts by weight, preferably 1 to 3 parts by weight.
  • concentration of components (a) and (b) in the composition of the present invention depends on the further components that are present in the composition.
  • compositions according to the present invention can advantageously be combined, in particular in cosmetic formulations (compositions), with further conventional components, such as, for example:
  • antimicrobial agents such as e.g. antibacterial agents or agents to treat yeast and mold, in particular those described in WO 2005/123101, antiacne and sebum reducing agents, in particular those described in WO 2008/046791, compounds against ageing of the skin, in particular those described in WO 2005/123101, antidandruff agents, in particular those described in WO 2008/046795, antiirritants (antiinflammatory agents, irritation-preventing agents, irritation-inhibiting agents), in particular those described in WO 2007/042472 and US 2006/0089413, antioxidants, in particular those described in WO 2005/123101, carrier materials, in particular those described in WO 2005/123101, chelating agents, in particular those described in WO 2005/123101, deodorizing agents and antiperspirants, in particular those described in WO 2005/123101, moisture regulators (moisture-donating agents, moisturizing substance, moisture-retaining substances), in particular those described in WO 2005/123101, moisture regulators (moisture-donating agents, moisturizing
  • odor from benzyl alcohol derivatives of formula (I) is clearly perceivable at such concentration levels with bitter almond and benzaldehyd-like odor facettes which are not desired in most cases (vide supra: odorless actives are preferred).
  • 2-methylbenzyl alcohol (o-tolyl alcohol) has a mild, floral, overall rosy, but also musty and sweet odor (n o 2957),
  • 4-methylbenzyl alcohol (p-tolyl alcohol) has a faint, green-rosy, leafy and sweet-balsamic odor (n o 2958).
  • benzyl alcohol derivatives of formula (I) can still play an important role in combating Aspergillus niger (as well as other germs).
  • the surprising finding is based on the fact that said benzyl alcohol derivatives of formula (I) do not have to be used in the high amounts needed when germs like Aspergillus niger are to be combated by the alcohol derivatives of formula (I) on their own, if said alcohol derivatives of formula (I) are combined with the compounds of component (b) of the present invention.
  • the benzyl alcohol derivatives of formula (I) are not used primarily as an antimicrobial agent being effective on its own, but rather they are used as an antimicrobial additive synergistically intensifying and enhancing the antimicrobial activity of the compounds of component (b).
  • the odor of the benzyl alcohol derivatives of formula (I) e.g. the odor of 4-methylbenzyl alcohol is not considered as being negative.
  • a composition of the present invention in addition to components (a) and (b) comprises a sensorially active amount of one or more fragrances of group (F) as stated below.
  • the presence of such fragrances leads to compositions (e.g. mixtures or other products) having improved odor properties.
  • compositions e.g. mixtures or other products
  • fragrances of group (F) in cosmetic compositions according to the present invention.
  • further components are generally present in the composition.
  • Group (F) of fragrances, from which one or more fragrances can be selected for combination with components (a) and (b) consists of (in the following list in some cases the normal industrial product names and registered trademarks of various firms are stated):
  • methyl dihydrojasmonate (preferably with a content of cis-isomers of >60 by weight, available under the names Hedione or Hedione HC),
  • alpha-ionone (4-(2,2,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
  • menthol preferably 1-menthol or racemic menthol, with particular preference for l-menthol
  • compositions are preferred comprising components (a) and (b) as defined above (preferably components (a) and (b) characterized above as being preferred), and in addition one, two or more fragrance compounds selected from group (F).
  • Such a preferred composition according to the present invention is preferably a cosmetic, pharmaceutical or oral care product, a foodstuff or a beverage, cosmetic products being particularly preferred.
  • compositions according to the invention in particular cosmetic products, comprising a sensorially active amount of one or more of the fragrances of group (F) lead to mixtures and products having improved odor properties.
  • compositions of the present invention comprising three, four, five or more of the fragrances selected from group (F) as stated above.
  • Such combinations can demonstrate an improved odor effect, see the examples section below.
  • fragrances of group (F) are selected from the group consisting of:
  • the total amount of the (preferred) fragrances from group (F) is in the range of from 0.01 to 1.5 wt.-%, more preferably in the range of from 0.05 to 1.0 wt.-%, most preferably in the range of from 0.1 to 0.75 wt.-%, based on the total weight of the composition.
  • compositions of the present invention include, in particular for a further improved effectiveness, one or more adjuvants selected from group (H) consisting of:
  • DPG dipropylene glycol
  • DEP diethyl phthalate
  • TEC triethyl citrate
  • IPM isopropyl myristate
  • BB benzyl benzoate
  • compositions according to the present invention comprising one or more cooling agents selected from the group consisting of: menthol, preferably l-menthol, menthone glycerin acetal (trade name: Frescolat®MGA), menthyl lactate (preferably l-menthyl lactate, in particular l-menthyl-l-lactate, trade name: Frescolat®ML), substituted menthyl-3-carboxylic acid amide (e.g.
  • menthyl-3-carboxylic acid-N-ethylamide menthyl-3-carboxylic acid-N-ethylamide
  • 2-isopropyl-N-2,3-trimethylbutanamide substituted cyclohexane carboxylic acid amide
  • 3-menthoxypropane-1,2-diol 2-hydroxyethylmenthylcarbonate, 2-hydroxypropylmenthylcarbonate
  • N-acetyl glycine menthyl ester Isopulegol, menthyl hydroxycarboxylic acid ester (e.g.
  • menthyl-3-hydroxybutyrate monomenthylsuccinate, 2-mercaptocyclodecanone, menthyl-2-pyrrolidin-5-one carboxylate, 2,3-dihydroxy-p-menthane, 3,3,5-trimethyl cyclohexanone glycerine ketal, 3-menthyl-3,6-di- and -trioxalkanoate, 3-menthylmethoxy acetate, N-(4-cyanomethylphenyl)-p-menthanecarboxamide, N-(4-cyanophenyl)-p-menthanecarboxamide and Icilin.
  • Preferred cooling agents are: l-menthol, menthone glycerine acetal (trade name: Frescolat®MGA), menthyl lactate (preferably l-menthyl lactate, in particular l-menthyl-l-lactate, trade name: Frescolat®ML), 3-menthoxy propane-1,2-diol, 2-hydroxyethyl menthyl carbonate, 2-hydroxypropyl menthyl carbonate, particular preference being for l-menthyl-l-lactate.
  • compositions according to the present invention may comprise one or more compatible solutes.
  • Preferred compatible solutes are described in WO 01/76572, namely dimyoinositol phosphate (DIP), diglycerin phospate (DGP), di-myo-inositol phosphate (DIP), cyclic 2,3 diphosphoglycerate (cDPG), 1,1-di-glycerol phosphate (DGP), beta-mannosyl glycerate (firoin), beta-mannosyl glyceramide (firoin-A) and di-mannosyl-di-inositol phosphate (DMIP) and ectoine and ectoine-derivatives, as described in EP 0 553 884, EP 0 671 161 and WO 94/15923, in particular ((S)-1,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) and hydroxyecto
  • the total amount of compatible solutes is in the range of from 0.05 to 10 wt.-%, preferably 0.1 to 5 wt.-%, based on the total weight of the formulation according to the present invention.
  • compositions according to the present invention may comprise one or more hair growth activators, i.e. agents to stimulate hair growth.
  • Hair growth activators are preferably selected from the group consisting of pyrimidine derivatives such as 2,4-diaminopyrimidine-3-oxide (Aminexil), 2,4-diamino-6-piperidinopyrimidine-3-oxide (Minoxidil) and derivatives thereof, 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine and its derivatives, xanthine alkaloids such as caffeine, theobromine and theophylline and derivatives thereof, quercetin and derivatives, dihydroquercetin (taxifolin) and derivatives, potassium channel openers, antiandrogenic agents, synthetic or natural 5-reductase inhibitors, nicotinic acid esters such as tocopheryl nicotinate, benzyl nicotinate and C1-C6 alkyl nicot
  • compositions according to the present invention may comprise one or more hair growth inhibitors, i.e. agents to reduce or prevent hair growth.
  • Hair growth inhibitors are preferably selected from the group consisting of activin, activin derivatives or activin agonists, ornithine decarboxylase inhibitors such as alpha-difluoromethylomithine or pentacyclic triterpenes like for example ursolic acid, betulin, betulinic acid, oleanolic acid and derivatives thereof, 5alpha-reductase inhibitors, androgen receptor antagonists, S-adenosylmethionine decarboxylase inhibitors, gamma-glutamyl transpeptidase inhibitors, transglutaminase inhibitors, soybean-derived serine protease inhibitors, extracts from microorganisms, algae, different microalgae or plants and plant parts of for example the families Leguminosae, Solanaceae, Graminae, Ascle
  • compositions according to the present invention may comprise one or more anti-cellulite agents as well as agents enhancing or boosting the activity of anti-cellulite agents.
  • Anti-cellulite agents and lipolytic agents are preferably selected from the group consisting of those described in WO 2007/077541, and beta-adrenergic receptor agonists such as synephrine and its derivatives.
  • Agents enhancing or boosting the activity of anti-cellulite agents are preferably selected from the group consisting of capsaicin and derivatives thereof, vanillyl-nonylamid and derivatives thereof, L-carnitine, coenzym A, isoflavonoides, soy extracts, ananas extract and conjugated linoleic acid.
  • compositions according to the present invention which in addition to components (a) and (b), in particular in addition to 1,2-alkanediols of component (b) (i), comprise one, two or more compounds of the group consisting of:
  • glycerol 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 2-methylpentane-2,4-diol, 2,5-hexanediol, 3,6-octanediol, 2-ethyl-1,3-hexanediol, 1,3-octanediol, and 1,3-decanediol.
  • compositions can be cosmetic, pharmaceutical or oral compositions, food stuffs or beverages.
  • composition according the present invention is to be used for preserving organic material, or if a composition according to the present invention in addition to components (a) and (b) comprises an organic material which is to be preserved, the composition preferably comprises one or more preservatives which do not belong to components (a) and (b).
  • additional preservatives are preferably selected from the group consisting of:
  • propionic acid and its esters and salts salicylic acid and its esters and salts, formaldehyde and paraformaldehyde, 2-hydroxybiphenyl ether and its salts, 2-zinc-sulfidopyridine N-oxide, inorganic sulfites and bisulfites, sodium iodate, chlorobutanolum, 4-ethylmercury-(II)5-amino-1,3-bis(2-hydroxybenzoic acid), its salts and esters, dehydracetic acid, formic acid, 1,6-bis(4-amidino-2-bromophenoxy)-n-hexane and its salts, the sodium salt of ethylmercury-(II)-thiosalicylic acid, phenylmercury and its salts, 10-undecylenic acid and its salts, 5-amino-1,3-bis(2-ethylhexyl)-5-methylhexahydropyrim
  • compositions of the present invention in addition to components (a) and (b) may additionally comprise further known antimicrobials like chitosan, totarol, farnesol, glycerol monolaurate, arylalkyl alcohols, such as e.g. 4-methyl-4-phenyl-2-pentanol and its derivatives (DE 101 43 434, in particular 4-methyl-4-phenyl-2-pentanol), muguet alcohol (2,2-dimethyl-3-phenylpropanol), other arylalkyl alcohols (e.g. as disclosed in DE 44 47 361, DE 103 30 697, U.S. Pat. No.
  • further known antimicrobials like chitosan, totarol, farnesol, glycerol monolaurate, arylalkyl alcohols, such as e.g. 4-methyl-4-phenyl-2-pentanol and its derivatives (DE 101 43 434, in particular 4-methyl-4-phenyl-2
  • compositions according to the present invention because of their synergistically intensified antimicrobial activity can in particular be employed
  • compositions according to the invention display their synergistically intensified antimicrobial action against a large number of Gram-positive bacteria, Gram-negative bacteria, moulds and yeasts.
  • a particularly good action exists against Propionibacterium acnes , Gram-positive bacteria such as Staphylococcus aureus, Staphylococcus epidermidis, Corynebacterium xerosis , Gram-negative bacteria, such as Escherichia coli and Pseudomonas aeruginosa , against yeasts, such as Candida albicans, Malassezia species (e.g. Malassezia furfur ), Epidermophyton species (e.g. Epidermophyton floccosum ), Trichophyton species (e.g.
  • compositions according to the invention against Aspergillus niger , a mould which can be combated only with great difficulty, is to be regarded as particularly advantageous here.
  • the present invention also relates to compositions of the present invention as a medicament, i.e. relates to the finding that compositions according to the present invention can be used for the therapeutic treatment of germs (as listed above).
  • compositions of the present invention for use in the treatment of germs, in particular for use in the treatment of Aspergillus niger.
  • the present invention relates to the use of compositions according to the present invention for the preparation of a medicament for use in the treatment of germs, in particular for use in the treatment of Aspergillus niger.
  • the invention also relates to the use of compositions according to the present invention as antimicrobial active compositions.
  • compositions according to the present invention apply mutatis mutandis to uses of compositions according to the present invention, and corresponding methods.
  • the present invention also relates to the use of (a) one, two or more compounds selected from the group consisting of benzyl alcohol derivatives of the formula (I)
  • each of the substituents R 1 , R 2 , and R 3 has a position at the aromatic ring, and wherein the substituents R 1 , R 2 , and R 3 independently of one another are selected from the group consisting of: H; OH; OCH 3 ; COON; linear or branched, saturated aliphatic hydrocarbon radical having 1 to 8 carbon atoms; linear or branched, unsaturated aliphatic hydrocarbon radical having 2 to 8 carbon atoms; COOR 4 , wherein R 4 is a linear or branched alkyl radical having 1 to 8 carbon atoms; wherein the total number of carbon atoms in substituents R 1 , R 2 and R 3 is 1 to 12, for synergistically intensifying the antimicrobial activity of (b) one, two or more compounds selected from the group consisting of:
  • the invention also relates to a method for synergistically intensifying the antimicrobial activity of
  • each of the substituents R 1 , R 2 , and R 3 has a position at the aromatic ring, and wherein the substituents R 1 , R 2 , and R 3 independently of one another are selected from the group consisting of: H; OH; OCH 3 ; COON; linear or branched, saturated aliphatic hydrocarbon radical having 1 to 8 carbon atoms; linear or branched, unsaturated aliphatic hydrocarbon radical having 2 to 8 carbon atoms; COOR 4 , wherein R 4 is a linear or branched alkyl radical having 1 to 8 carbon atoms; wherein the total number of carbon atoms in substituents R 1 , R 2 and R 3 is 1 to 12.
  • the invention also relates to a method for the preservation or antimicrobial treatment of a perishable product, with the following step:
  • the present invention furthermore relates to corresponding methods for the cosmetic and/or therapeutic treatment of germs, and in particular especially of (a) microorganisms which cause body odor, (b) microorganisms which cause acne (c) microorganisms which cause mycoses, (d) microorganisms which cause dandruff, comprising topical application of an antimicrobially active amount of a composition according to the invention, the amount of said diols and benzyl alcohol derivatives in the composition preferably being adjusted such that their antimicrobial action is synergistically intensified.
  • Preferred embodiments of the methods and uses according to the present invention correspond to the preferred embodiments of the compositions according to the present invention, which are explained above and below.
  • the human skin is populated by a large number of various microorganisms, which include the microorganisms already mentioned above, as well as others. Most of these microorganisms are not pathogenic and are irrelevant to the physiological state of the skin and to the odor thereof. On the other hand, others can influence the healthy state of the skin decisively.
  • the synergistically active compositions of the present invention have a good antimicrobial activity not only against Aspergillus niger but also against Staphylococcus epidermidis, Corynebacterium xerosis, Brevibacterium epidermidis, Propionibacterium acnes and against Trichophyton and Epidermophyton species, so that they can also be employed as agents for the treatment of (combating) underarm and foot odor or body odor generally, as agents for combating acne, as antidandruff agents and for the treatment of mycoses (in particular dermatomycoses).
  • treatment is understood as meaning any form of influencing of the microorganisms in question in which the multiplication of these microorganisms is inhibited and/or the microorganisms are killed.
  • the total amount of components (a) and (b) in compositions of the present invention, in particular in cosmetic, pharmaceutical or oral care products or in a foodstuff or beverage, is preferably in the range of from 0.01 to 10 wt.-%, but particularly preferably in the range of from 0.05 to 5 wt.-%, based on the total weight of the product, foodstuff or beverage.
  • the total amount of component (a) can be in the range of from 0.05 to 0.5 wt.-%, based on the total weight of the product, foodstuff or beverage. This is advantageous since such a reduced amount of compounds of group (a) results in a reduced odor impression stemming therefrom.
  • the product, foodstuff or beverage comprises conventional further constituents, in this context see below.
  • the particular content of components (a) and/or (b) to be used according to the invention in compositions according to the invention can be below the amount regarded as antimicrobially active in itself if the total amount of these substances which is present is sufficiently high to achieve an antimicrobial action of the total mixture. This applies in particular to the action against Aspergillus niger.
  • the invention also relates to a method for the cosmetic and/or therapeutic treatment of (a) microorganisms which cause body odor, (b) microorganisms which cause acne and/or (c) microorganisms which cause mycoses (d) microorganisms which cause dandruff, wherein said microorganisms are brought into contact with an antimicrobially active amount of a composition according to the present invention.
  • the total amount of components (a) and (b) of the composition used within the method of the present invention is preferably in the range of from 0.01 to 10 wt.-%, and particularly preferred in the range of from 0.05 to 5 wt.-%, based on the total weight of the (cosmetic or pharmaceutical) composition which comprises the mixture of components (a) and (b).
  • compositions according to the present invention comprising the synergistically active mixture of components (a) and (b), can be employed prophylactically or as required.
  • the total amount of components (a) and (b) to be applied i.e. the total amount of the composition according to the present invention to be applied e.g. daily, varies and depends on the physiological state of the subject and individual-specific parameters, such as age or body weight.
  • the mixture of components (a) and (b) can be employed either by themselves or in combination with further antimicrobially active substances.
  • the 1,2-alkanediols of sub-group (b) (i) in compositions according to the present invention can be in the form of either the corresponding enantiomer of 2S configuration or the enantiomer of 2R configuration and in the form of any desired mixture of these enantiomers of 2S and 2R configuration.
  • racemates of the particular 1,2-alkanediols to be employed or mixtures of two or more racemates
  • the racemates are particularly readily accessible by synthesis, but the pure enantiomers or non-racemic mixtures of these enantiomers are likewise suitable for the purposes according to the invention.
  • compositions comprising components (a) and (b), especially if employed against germs which cause body odor, are as a rule applied topically in the form of solutions, creams, lotions, gels, sprays or the like.
  • an oral (tablets, capsules, powders, drops) intravenous, intraocular, intraperitoneal or intramuscular administration or an administration in the form of an impregnated dressing is appropriate in some cases.
  • Mixtures of components (a) and (b) can be incorporated without difficulties into the usual cosmetic and/or dermatological formulations, such as, inter alia, pump sprays, aerosol sprays, creams, ointments, tinctures, lotions, nail care products (e.g. nail varnishes, nail varnish removers, nail balsams) and the like. It is also possible here, and in some cases advantageous, to combine the mixture of components (a) and (b) with further active compounds, for example with other antimicrobially, antimycotically or antivirally active substances.
  • Cosmetic and/or dermatological/keratological compositions comprising components (a) and (b) can otherwise have the conventional chemical composition, and might serve for the treatment of skin and/or hair in the sense of a dermatological treatment or a treatment in the sense of care cosmetics.
  • compositions of the present invention can also be employed in make-up products in decorative cosmetics.
  • components (a) and (b) can moreover also particularly advantageously be employed in combination with perspiration-inhibiting active compounds (antiperspirants) for combating body odor.
  • Perspiration-inhibiting active compounds which can be employed are, above all, aluminium salts, such as aluminium chloride, aluminium hydrochloride, nitrate, sulfate, acetate etc.
  • the use of compounds of zinc, magnesium and zirconium may also be advantageous.
  • the aluminium salts and—to a somewhat lesser extent—aluminium/zirconium salt combinations have essentially proved suitable.
  • the aluminium hydroxychlorides which are partly neutralized and therefore tolerated better by the skin, but not quite so active, are additionally worth mentioning.
  • compositions of the present invention if components (a) and (b) are used for antimicrobial treatment of a surface (e.g. of a human or animal body), a combination with (metal) chelators is advantageous in some cases.
  • (Metal) chelators which are preferably to be employed here are, inter alia, ⁇ -hydroxy fatty acids, phytic acid, lactoferrin, ⁇ -hydroxy acids, such as, inter alia, citric acid, lactic acid and malic acid, and humic acids, bile acids, bile extracts, bilirubin, biliverdin or EDTA, EGTA and derivatives thereof.
  • compositions according to the present invention in the form of cosmetic and/or dermatologically active compositions are applied to the skin and/or hair in a sufficient amount in the conventional manner for cosmetics and dermatics.
  • cosmetic and dermatological compositions which comprise components (a) and (b) and additionally act as sunscreen compositions offer particular advantages.
  • These compositions (formulations) advantageously comprise at least one UVA filter and/or at least one UVB filter and/or at least one inorganic pigment.
  • the compositions can be in various forms such as are conventionally employed e.g. for sunscreen formulations. They can be e.g.
  • a solution an emulsion of the water-in-oil (W/O) type or of the oil-in-water (O/W) type or a multiple emulsion, for example of the water-in-oil-in-water (W/O/W) type, a gel, a hydrodispersion, a solid stick or also an aerosol.
  • compositions which comprise components (a) and (b) can advantageously be combined with substances which absorb UV radiation, the total amount of the filter substances being e.g. 0.01 to 40 wt.-%, preferably 0.1 to 10 wt.-%, in particular 1.0 to 5.0 wt.-%, based on the total weight of the formulations, in order to provide cosmetic compositions which protect the hair or skin from ultraviolet radiation.
  • compositions of the present invention comprising components (a) and (b) in a mixture, in particular compositions comprising 4-methylbenzyl alcohol, preferably in combination with 1,2-pentanediol, 1,2-hexanediol, 1,2-octanediol and 1,2-decanediol or mixtures of said 1,2-alkanediols have also an excellent antimicrobial activity against yeasts, in particular against Candida albicans and moulds, in particular against Aspergillus niger.
  • compositions of the present invention are sunscreen formulations in the form of aqueous emulsions, preferably of the water-in-oil (W/O) or of the oil-in-water (O/W) type or a multiple emulsion, for example of the water-in-oil-in-water (W/O/W) type, more preferably of the oil-in-water (O/W) type.
  • Preferred sunscreen formulations (compositions) of the present invention comprise a total amount of organic UV filters of greater than 10 wt.-%, preferably in the range of from 12 to 40 wt.-%, more preferred in the range of from 15 to 35 wt.-%, based on the total weight of the sunscreen formulation.
  • Organic UV filters which are particularly preferred in compositions of the present invention (in particular if they are in the form of a sunscreen formulation), preferably in an amount mentioned (above), are:
  • compositions according to the present invention in the form of sunscreen formulations preferably have a SPF (sun protection factor) of equal or greater than 15, preferably of equal or greater than 20, more preferably of equal or greater than 30.
  • compositions of the present invention in the form of sunscreen formulations comprise 4-(1,1-dimethylethyl)-4′-methoxydibenzoylmethane(4-t-butyl-4′-methoxydibenzoyl methane; avobenzone), preferably in an amount in the range of from 0.2-10 wt.-%, more preferred in the range of from 0.5-5 wt.-%, based on the total weight of the sunscreen formulation.
  • the pH-value is in the range of from pH 4 to pH 8, preferably from pH 4 to 6.5.
  • compositions of the present invention in the form of formulations for topical prophylactic or cosmetic treatment of the skin a high content of care substances is generally advantageous.
  • the compositions comprise one or more animal and/or plant fats and oils having care properties, such as olive oil, sunflower oil, refined soya oil, palm oil, sesame oil, rapeseed oil, almond oil, borage oil, evening primrose oil, coconut oil, shea butter, jojoba oil, sperm oil, beef tallow, neat's foot oil and lard, and optionally further care constituents, such as, for example, fatty alcohols having 8 to 30 carbon atoms.
  • care substances can be combined in an outstanding manner with the admixture of components (a) and (b).
  • Such care substances include
  • compositions of the present invention which are cosmetic compositions (formulations) in some cases preferably comprise antioxidants. All antioxidants can be used which are suitable or usual for cosmetic and/or dermatological uses.
  • Cosmetic compositions of the present invention which comprise an admixture of components (a) and (b) can additionally comprise vitamins and vitamin precursors.
  • All vitams and vitamin precursors can be used which are suitable or usual for cosmetic and/or dermatological uses.
  • vitamins and vitamin precursors such as tocopherols, vitamin A, niacic acid and niacinamide, further vitamins of the B complex, in particular biotin, and vitamin C and panthenol and derivatives thereof, in particular the esters and ethers of panthenol and cationically derivatized panthenols, such as e.g. panthenol triacetate, panthenol monoethyl ether and the monoacetate thereof and cationic panthenol derivatives.
  • Cosmetic compositions of the present invention can also comprise antiinflammatory or redness- or itching-alleviating active compounds. All antiinflammatory or redness- and itching-alleviating active compounds can be used which are suitable or usual for cosmetic and/or dermatological uses.
  • Cosmetic compositions of the present invention can also comprise active compounds having a skin-lightening or skin-tanning action. All skin-lightening or skin-tanning active compounds can be used which are suitable or usual for cosmetic and/or dermatological uses.
  • Cosmetic compositions according to the present invention can also comprise anionic, cationic, nonionic and/or amphoteric surfactants, especially if crystalline or microcrystalline solids, for example inorganic micropigments, are to be incorporated into the composition.
  • DPG dipropylene glycol
  • IPM isopropyl myristate.
  • Testing thus comprises contamination of the formulation, if possible in its final condition, with a prescribed inoculum of suitable microorganisms, storage of the inoculated formulation at a certain temperature, removal of samples from the container at certain intervals of time and determination of the number of microorganisms in the samples removed in this way.
  • the preserving properties are adequate if, under the conditions of the test, a clear reduction or, where appropriate, no increase in the germ count results in the inoculated formulations after the prescribed times at the prescribed temperatures.
  • Experimental details of the test procedure are described in the European Pharmacopoeia (ISBN 3-7692-2768-9; Supplement 2001 to the 3rd Edition, page 421-422, chapter 5.1.3).
  • microorganism strains were used for the tests for adequate preservation:
  • the initial germ count (cfu/ml; “0 value”) was in the range of from 230000 to 400000 in the various test series.
  • microorganism strains were used for the tests for adequate preservation:
  • the initial germ count (cfu/ml; “0 value”) was in the range of from 230000 to 400000 in the various test series.
  • microorganism strains were used for the tests for adequate preservation:
  • the initial germ count (CFU/g; “0 value”) was in the range of from 230000 to 400000 in the various test series.
  • A2 is the comparison formulation comprising Phenonip® (not according to the present invention).
  • Phenonip® is a commercially available (Clariant, Nipa preservatives) and in cosmetic formulations widely used antimicrobial active mixture consisting of phenoxyethanol, methylparaben, ethylparaben, butylparaben, propylparaben and isobutylparaben.
  • C8-4MBA is a composition according to the present invention comprising 0.50 wt.-% 1,2-octanediol and 0.5 wt.-% 4-methylbenzyl alcohol.
  • the initial germ count (cfu/ml; “0 value”) was in the range of from 200,000 to 400,000 in the various test series.
  • efficient preservation with mixtures according to the invention is even achieved for very difficult to preserve cosmetic formulations with a high amount of organic UV filters and having a SPF of equal or greater than 15.
  • An at least 3 log reduction was achieved for yeast ( Candida albicans ) and an almost 2 log reduction was achieved for mold ( Aspergillus niger ) after 7 days.
  • An at least 3 log reduction was also achieved for bacteria ( Pseudomonas aeruginosa, Staphylococcus aureus, Escherichia coli ) after 2 days.
  • Formulation F1 Sunscreen Lotion (According to the Present Invention)
  • Formulation F2 Silicone Emulsion (According to the Present Invention)
  • Formulation F3 W/O Sunscreen Lotion (According to the Present Invention)
  • Formulation F4-F13 Cosmetic formulations comprising a sufficient antimicrobial active amount of
  • At least one 1,2-alkanediol at least one 1,2-alkanediol.
  • Solubilizer PEG-40 Hydrogenated 2.0 (Symrise) Castor Oil, Trideceth-9, Water (Aqua) Sun Flower Oil Helianthus Annuus 5.0 (Wagner) (Sunflower) Seed Oil Sweet Almond Prunus dulcis 5.0 Oil (Wagner) SymMatrix Maltodextrin, 0.1 0.3 1.0 (Symrise) Rubus Fruticosus (Blackberry) Leaf Extract Fragrance of Fragrance 0.3 0.3 0.3 0.2 0.4 0.4 0.5 0.3 0.3 1.0
  • Formulation 14-23 Cosmetic formulations comprising a sufficient antimicrobial active amount of
  • At least one 1,2-alkanediol at least one 1,2-alkanediol.

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US20110152383A1 (en) 2011-06-23
EP2306820A2 (fr) 2011-04-13
WO2008119841A3 (fr) 2009-09-11
WO2008119841A2 (fr) 2008-10-09
CN107410304A (zh) 2017-12-01
BRPI0822929B8 (pt) 2021-05-25
CN102123585A (zh) 2011-07-13
JP2011527294A (ja) 2011-10-27
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JP5588435B2 (ja) 2014-09-10
BRPI0822929B1 (pt) 2021-04-13

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